2-Chloronicotinonitrile → (S)-N-(1-{4-[1-(3-Cyanopyridin-2-yl)piperidin-4-yl]phenyl}ethyl)acetamide

HRID 1470746Notes

Reaction equation

CCN(C(C)C)C(C)C.Cl[C:11]1[N:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].[NH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28]([C@@H:31]([NH:33][C:34](=[O:36])[CH3:35])[CH3:32])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>CN1C(=O)CCC1>[C:13]([C:12]1[C:11]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][C:28]([C@@H:31]([NH:33][C:34](=[O:36])[CH3:35])[CH3:32])=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[N:18][CH:17]=[CH:16][CH:15]=1)#[N:14]

Participants

Conditions

Temperature: 130 °C

Procedure

50 μL (0.29 mmol) DIPEA are added to a mixture of 14 mg (0.10 mmol) 2-chloronicotinnitrile and 29 mg (0.11 mmol) (S)-N-[1-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) in 1.45 mL NMP. The mixture is stirred at 130° C. overnight. Subsequently the solvent is removed in vacuo, the residue is taken up in DMF and the mixture is purified using reversed phase HPLC (water/MeOH, 0.1% TFA) to yield the desired product.

Workup

customSubsequently the solvent is removed in vacuo
customthe mixture is purified

Sources & evidence

ORD record: ord-9a04e1e5250547cf86f6299edc8eb6b4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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